Chlorosuccinimide → 2-Methyl-N-[4-(1-chloropyrrolo[1,2-a]quinoxalin-5(4H)-ylcarbonyl)phenyl]benzamide

HRID 1456058

Reaction equation

HRID 1456058 reaction equation
[CH3:1][C:2]1[CH:31]=[CH:30][CH:29]=[CH:28][C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]([N:15]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[N:18]3[CH:25]=[CH:26][CH:27]=[C:17]3[CH2:16]2)=[O:14])=[CH:9][CH:8]=1)=[O:5].[Cl:32]N1C(=O)CCC1=O>O1CCCC1>[CH3:1][C:2]1[CH:31]=[CH:30][CH:29]=[CH:28][C:3]=1[C:4]([NH:6][C:7]1[CH:8]=[CH:9][C:10]([C:13]([N:15]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[N:18]3[C:25]([Cl:32])=[CH:26][CH:27]=[C:17]3[CH2:16]2)=[O:14])=[CH:11][CH:12]=1)=[O:5]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 153406682-Methyl-N-[4-(pyrrolo[1,2-a]quinoxalin-5(4H)-ylcarbonyl)phenyl]benzamide

Product 1

HCID 218369702-Methyl-N-[4-(1-chloropyrrolo[1,2-a]quinoxalin-5(4H)-ylcarbonyl)phenyl]benzamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To an ice-water cooled suspension of 5 mmol of 2-methyl-N-[4-(pyrrolo[1,2-a]quinoxalin-5(4H)-ylcarbonyl)-phenyl]benzamide in 5 ml of tetrahydrofuran is added 5.5 mmol of N-chlorosuccinimide followed by continued stirring in the cold for 10 minutes. The bath is removed and stirring continued for 2.25 hours. The reaction mixture is added to ice-water and extracted with ether. The organic layer is dried and concentrated in vacuo to give the desired product as a solid.

Workup

  1. customThe bath is removed
  2. stirringstirring
  3. waitcontinued for 2.25 hours
  4. additionThe reaction mixture is added to ice-water
  5. extractionextracted with ether
  6. customThe organic layer is dried
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b703e91a73b54fc3b223880f6b704612
Source dataset
uspto-grants-1998_12
Patent number
US05843944

Linked notes

Loading…